Spiro-orthocarbonate compounds and methods of making them are known. For example, a method resorting to the reaction of bis(tributyltin)-alkylene glycolates with carbon disulfide disclosed in Journal of Organic Chemistry, 35, 2347 (1970) and a method relaying on the reaction of dialkyl-tin cyclic dialkoxides with carbon disulfide disclosed similarly in Journal of Organic Chemistry, 36, 1176 (1971) are known for the production of such compounds. The latter method may be expressed by reaction formulas as follows: ##STR2## wherein (A) represents a polymethylene group or an alkyl substituent thereof and R' represents an alkyl group.
The above described conventional methods use, as raw materials, organic tin compounds which are not ordinary commercial products and carbon disulfide which is too toxic to permit easy handling. The reactions involved therein are complicated and the products of these reactions are extremely difficult of isolation. Thus, these methods entail various problems. Accordingly, these methods are not feasible for the commercial production of spiroorthocarbonates.
It has been known to produce cyclic acetals by the reaction of aldehydes or ketones and alkylene oxides, as described in G. Willfang, Ber. 74, 145 (1941) and M.T. Bogert et al, J. Am. Chem. Soc., 55, 3741 (1933). On the other hand, it has also been known that cyclic carbonates exhibit quite different reactivity and reaction behavior from those of aldehydes or ketones though cyclic carbonates have a carbonyl group as well as aldehydes and ketones. For example, ketones react with mercaptans, amines or hydrogen cyanide to produce mercaptols or cyanohydrines, whereas cyclic carbonates do not react or are decomposed to produce dioxide gas and quite different compounds such as thioethers, .beta.-hydroxyethylamin, etc., and further cyclic carbonates react with phenols, diamines, urea, carboxylic acids, etc., though ketones do not react with such compounds or they react in quite different behavior.